Toxaphene

Toxaphene (approximate overall empirical formula of C10Hi0C15) is a persistent, broad-spectrum insecticide with some occurrence in drinking water. Its registered uses are currently limited. The EPA reported that toxaphene is highly persistent and accumulates in the environment. Acute exposure to toxaphene affects various organs in humans. Toxaphene has been classified in the EPA s Group B2 (probable human carcinogen). 

Eisler, R. 2000. Toxaphene. Pages 1459-1481 in Handbook of Chemical Risk Assessment Health Hazards to Humans, Plants, and Animals. Volume 2, Organics. Lewis Publishers, Boca Raton, Flmda. 

Eisler, R. and J. Jacknow. 1985. Toxajdiene hazards to fish, wildlife, and invertebrates a synt tic review. UJS. Fish WUdl. Serv. Biol. Rep. 85(1.4), 26 pp. 

Because toxaphene consists of numerous compounds, it seems inappropriate and misleading to continue using the name toxaphene to describe this insecticide. It is known that chemical properties, such as solubility, toxicity, volatility, and other properties, are the sum of the individual contributions of many different compounds in differing relative amounts. A 50-fold difference between toxicides of toxaphene components can occur, and, with a wide range in the polarity of different fractions, there prohahly are also significant solubility differences. In addition, the composition of toxaphene changes with time, and residues in fat are not of the same coinxtsition as parent toxaphene. The metabolism of toxaphene 

Toxaphene elimination rates vary between species. In rats, the half-time persistence of toxaphene (time to 50% excretion = Tbl/2) was 1-3 days. If the trend persisted, virtually all toxaphene would be eliminated in about 15 days. Elevated blood toxaphene levels in a human subject who had eaten catfish fillets containing 52.0 mg of toxaphene/kg dropped 67% in 11 days. By 14 days after the initial measurement, toxaphene blood levels were below analytical detection limits. Persistence seems to be longer in some fishes. Lake trout (Salvelinus namaycush) given a single intraperitoneal injection of 7.0 mg toxaphene/kg body weight (BW) had a Tbl/2 of 322 days for white suckers (Catostorms commersoni) this value was 524 days. 

IUPAC name A reaction mixture of chlorinated camphenes containing 67-69% chlorine 

Uses Toxaphene is a yellow to amber, waxy solid that smells like turpentine. It does not bum and readily changes to vapor when in solution. Toxaphene in soil vaporizes to air or stick or soil particles. Toxaphene is a mixture containing more than 670 chemicals.12,14 

Toxaphene was one of the most heavily used insecticides in the United States until most uses were banned in 1982 by the USEPA. Toxaphene was used primarily in the southern United States to control insect pests on cotton and other agricultural crops. It also was used to control insect pests on livestock and to kill 

Toxaphene is a very stable, persistent, solid compound that requires decades to break down into different components. In fact, nearly 45% of the toxaphene applied to the soil in 1951 was detected 20 years later. Toxaphene has very low solubility in water, but in organic solvents, it is miscible. Toxaphene is very volatile and quickly changes to vapor, which transmigrates in the atmosphere to very long distances. Reports indicate that toxaphene bioaccumulates, rapidly breaks down in the intact body of animals, and eventually discharges out.68 

Toxicity The acute oral LD50 and dermal LD50 toxicity of toxaphene in rats are 40 and 600 mg/kg, respectively. Toxaphene is an active nerve poison and interferes with fluxes of cations across nerve cell membranes, which increases neuronal irritability and results in convulsions and seizures. Toxaphene also has been found to damage the lungs, liver, and kidney of animals and humans. Although the dermal adsorption efficiency of toxaphene is less than that of other organochlorines, its absorption is enhanced by fat and fat solvents. Toxaphene has been shown to cause cancer in pregnant animals and to induce birth defects.68 

Empirical formula CioHioClg, a complex mixture of a large number of Cio chloroderi-vatives of camphene CAS [8001-35-2] UN 2761 

Yellow wax-like solid mild pleasant odor density 1.63 g/cm melts at 65-90°C 

Moderately toxic by ingestion mild skin irritant animal experiments indicate sufficient evidence of carcinogenicity cancer-causing effects in humans remain unknown. 

Studies on the cancer risk assessment of toxaphene in rodents have shown that it increased incidence of neoplasms of endocrine organs, thyroid, pitnitary, adrenal and mammary glands and reproductive systems (Buranatrevedth 2004). 

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Mode of Motion. The cyclodienes, like lindane and toxaphene, affect the nerve axon produciag hyperactivity, convulsions, prostration, and death. The biochemical lesion is the competitive inhibition of the y-aminobutyric acid (GABA) neurotransmitter binding site of the nerve axon. Spray workers with lengthy exposure to dieldrin have suffered from prolonged and repeated central nervous system disturbances produciag epileptiform coavulsioas. Similar disturbances occurred ia workers heavily exposed to chlordecoae. 

Chlorinated Terpenes. A group of incompletely characterized insecticidal compounds has been produced by the chlorination of the naturally occurring terpenes. Toxaphene [8001-35-2] is prepared by the chlorination of the bicycHc terpene, camphene [79-92-5] to contain 67—69% chlorine and has the empirical formula C QH QClg. The technical product is a yellowish, semicrystalline gum (mp 65—90°C, d 1.64) and is a mixture of 175 polychloro... 

Much controversy has arisen regarding the ability of mixtures of weakly estrogenic compounds to act synergistically, notably the synergistic potential of mixtures of PCBs or of the insecticides dieldrin and toxaphene. " Recent studies suggest that the action of mixtures is at least additive. "... 

A number of other chemicals suspected of having endocrine disrupting potential also occur at high levels in the tissues of marine mammals. For example, tribiityltin compounds are present in the tissues of the Steller sea lion (Eumetopias juhatus) from Hokaido, Japan, and in stranded bottlenose dolphins (Tursiops truncatus) found along the US Atlantic and Gulf coasts.Additional chemicals detected include PAHs, toxaphene and chlordane. ... 

Chlorinated camphene (toxaphene) Chlorinated diphenyl oxide Chlorine... 

Toxaphene zero 0.003 Kidney, liver, or thyroid problems increased risk of cancer Runoff/leaching from insecticide used on cotton and cattle... 

Bromophenol blue (3.0...4.6) aliphatic carboxylic acids [225 — 228] malonic and lactic acids [229] palmitic and lactic acids [230] malonic, glycolic, malic, citric, tartaric, ketoglutaric, galacturonic and oxalic acids [196] dicarboxylic acids, succinic acid [231] indoleacetic acid, trichloroacetic acid [232] palmitic acid, palmityl- and stearyllactic acid [223] benzoic, sorbic and salicylic acid [234] metabolites of ascorbic acid [235] chloropropionic acid [236] oligogalacturonic acids [237] amino acids, hydrocarbons, mono-, di- and triglycerides [238] xylobiose, xylose, glucose and derivatives [239] sugar alcohols [91] toxaphene [240]... 

D. Hainzl, J. Burhenne and H. Pariar, HRGC-ECD and HRGC-NICI SIM quantification of toxaphene residues in selected marine organism by envir onmentally relevant chloroboT nanes as standard , Chemosphere 2S 237-243 (1994). 

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